Sodium Hydroxide → 3-[(Dibutylamino)methyl]phenol

Participants

Reaction Steps

A mixture of 33.0 g (0.133 m) of 3-acetoxy-N,N-dibutylbenzamide in 400 ml of ether was slowly added over one half hour to a suspension of 5.0 (0.133 m) grams of lithium aluminum hydride (LAH) in 300 ml of ether. The mixture was heated to reflux for 2 hours. The mixture was slowly treated with 5.0 ml of water, 5.0 ml of 15% sodium hydroxide and 15.0 ml of water. Magnesium sulfate was added and stirred well. The mixture was filtered and washed well with ether. The solvent was evaporated off leaving the 3-hydroxy N,N-dibutylbenzylamine product in a yield of 23.3 g. The product was a yellow oil with a refractive index of n(25/D)=1.5172.

Provenance & Evidence